Organic insecticide and its use



Patented Aug. 27, 1940 ORGANIC INSECTICIDE AND ITS USE James William SwainaBayside, N. Y., assignor to General Chemical Company,

New York,

N. Y., a corporation of New York No Drawing. Application November 23, 1938, Serial No. 241,935

22 Claims.

This invention relates to insecticides. It is particularly directed to a new class of insecticidal compounds for combatting an unusually wide variety of insects.

The insecticides of the present invention may be usedas stomach poison insecticides in combatting chewing insects, such as the larvae of moths and butterflies, larval and adult beetles, grasshoppers and crickets, insects which feed on exposed liquids and solids such as the housefly and'fruitflies, and insects such as thrips which lacerate the epidermis of plants and suck up the exuding sap. 0n the other hand, they may be used as contact insecticides against sucking insects such as green and brown chrysanthemum aphids, green peach aphids, kale aphids, and green cabbage aphids.

The insecticides of the present invention are organic compounds containing not less than eight andnot more than eighteen carbon atoms and are characterized by the common nucleus represented by the general formula:

wherein R1 represents a furyl or phenyl radical, R2 represents H or an alkyl (CnH2n+]-) or acyl radical, and R3 represents (a) an open, straight or branched carbon chain, which may contain one or more carbon atoms, or (b) a phenyl, a naphthyl, or a furyl radical, or (c) a mixed radical consisting of an open, straight or branched carbon chain (a) and a phenyl, naphthyl, or furyl group (b).

When employed against chewing and similar insects as stomach poisons, the insecticides of the present invention may be applied to fruit, foliage, or other food of the insect to be combatted. When employed as contact insecticides, they may be sprayed directly upon the insects.

The insecticides of the present invention are compatible with and therefore may be used in compounds within the purview of the present invention, demonstrate the efliciency of the new insecticides in combatting insects in general. Each compound was tested against one or more types of insects and was employed as a solution or a suspension in a suitable liquid medium. Tests upon aphids were conducted by spraying leaves, upon which aphids were feeding, with the solution or suspension of insecticide and counting dead and live aphids at the end of 24 hours. Tests upon codling moth larvae were conducted by spraying fruit with the solution of insecticide, draining, applying larvae to the treated fruit and counting dead and live larvae at the end of 24 hours. BTW designates a benzene, triethanola mine-oleate, water suspension prepared by dissolving the compound in a minimal quantity of benzene, about 1 /2 cc. for each to 1 gram of compound, adding the solution to a suspension of about 1 /2 cc. of triethanolamine-oleate in 20 cc. of water, and diluting with water to the indicated proportion. The letter A preceding the efliciency figure stands for brown chrysanthemum aphids, the letter B for green chrysanthemum aphids, the letter C for green cabbage aphids, the letter D for green peach aphids, and the letter E for codling moth larvae. Check tests were run in each case without insecticide.

The efficiency of control in the expression of results below is calculated as follows:

tained as follows: sac-22:68, 100 22=7s, and

68+78=.87, giving an efliciency of 87%.

Efficiency per cent Difurfural-acetone in BTW D 68 Difurfural-acetone in BTW A 80 Difurfural-acetone 1% in acetone E 93 Difurfural-acetone 1% in suspension in water E 61 Furfural-acetophenone A1% in BTW A.. 99 Furfural-acetophenone /8% in BTW A 92 Furfural-acetophenone in BTW A 89 Furfural-acetophenone A;% in BTW C Furfural methyl-n amyl ketone in BTW A 87 Furfural-methyl-n-amyl-ketone /8% in BTW Efliciency per cent Furfural-methyl-n-hexyl-ketone in BTW A 96 Furfural-methyl-n-hexyl-ketone in BTW A 96 Furfural-methyl-n-hexyl-keytone in 'C '70) Furfural-methyl-isobutyl-ketone 1% in A '77 Furfural-pinacoline 4% in BTW A 98 Benzal-acetophenone 7 in BTW A 93 Benzal-acetophenone 365% in BTW B 91 Benzal-acetophenone /2 in BTW D 91 Benzal-acetophenone 1% in acetone E 80 Benzal-benzyl-acetone 1% in acetone E The following additional compounds have been found to possess activity against codling moth larvae or aphids as indicated.

Furfural-acetone (E) 4-methoxy-benzalacetophenone (E), Furfural-beta-acetonaphthone (A) and (E), Benzal-pinacoline (A),

Furfural 2-methyl 5 isopropyl acetophenone Furfural-methyl-nonyl-ketone (C) l-furfural-propiophenone (A), l-furyl-2,2-diaceto-ethene (condensation product of a-furfural and acetyl-acetone) (C), Dibenzal-acetone (D),

Di- (m-nitrobenzal) -acetone (E) Furfural isopropylidene acetone (condensation product of u-furfural and mesityl oxide) (A).

I claim:

1. An insecticide comprising an organic compound containing not less than 8 and not more than 18 carbon atoms and consisting essentially of the nucleus:

R1C=C-CRx H R2 (I) R1 representing a furyl or phenyl radical, R2 representing H or an alkyl or acyl radical, and R3 representing a straight or branched carbon chain, a phenyl, a naphthyl, or a iuryl radical, or a mixed radical consisting of a straight or branched carbon chain and a phenyl, naphthyl, or furyl group. a

2. An insecticide comprising an organic compound containing only the elements carbon, hydrogen, and oxygen and containing not less than 8 and not more than 18 carbon atoms, and consisting essentially of the nucleus:

I I 11 R2 0 R1 representing a furyl or phenyl radical, R2 representing H or an alkyl or acyl radical, and R3 representing a straight or branched carbon chain, a phenyl, a naphthyl, or a furyl radical, or a mixed radical consisting of a straight or branched carbon chain and a phenyl, naphthyl, or furyl group.

3. An insecticide comprising an organic compound containing only the elements carbon, hydrogen, and oxygen and containing not less than 8 and not more than 18 carbon atoms, and consisting essentially of the nucleus:

R1 representing a furyl or phenyl radical, R2 representing H or an alkyl or acyl radical, and R3 representing a straight or branched carbon chain, a phenyl, a naphthyl, or a furyl radical,

or a mixed radical consisting of a straight or branched carbon chain and a phenyl, naphthyl, or furyl group, said compound being free from oxygen other than that in the keto group of the formula or in a furyl group.

4. An insecticide comprising difurfural-acetone.

5. An insecticide comprising furfural-acetophenone.

6. An phenone.

7. The method of combatting chewing insects, which comprises applying to the food 01' the insect an insecticide of the type defined by claim 1. I

8. The method of combatting chewing insects, which comprises applying to the food of the insect an insecticide of the type defined by claim 2.

9. The method of combatting chewing insects, which comprises applying to the food of the insect an insecticide of the type defined by claim 3.

10. The method of combatting codling moth larvae, which comprises applying to the food of the insect an insecticide of the type defined by claim 4. i

11. The method of,combatting codling moth larvae, which'comprises applying to the food of the insect an insecticide of the type defined by claim 6.

12. The method of combatting sucking insects, which comprises applying to the insect an insecticide of the type defined by claim 1.

13. The method of combatting sucking insects, which comprises applying to the insect an insecticide of the type defined by claim 2.

14. The mthod of combatting sucking insects, which comprises applying to the insect an insecticide of the type defined by claim 3.

15. The method of combatting brown chrysanthemum aphids, which comprises applying to the aphids an insecticide comprising difurfuralacetone.

16. The method of combatting aphids, which comprises applying to the aphids an insecticide comprising furfural-acetophenone.

17. The method of combatting aphids, which comprises applying to the aphids an insecticide comprising benzal-acetophenone.

18. An insecticide comprising an organic cominsecticide comprising benzal-acetopound containing not less than 8 and not more 1' than 18 carbon atoms and consisting essentially of the nucleus:

R1 representing a furyl or phenyl radical, R2 representing H or an alkyl or acyl radical, and R3 representing a carbon chain, a phenyl, a naphthyl, or a furyl radical, or a mixed radical consisting of a carbon chain and a phenyl or JAMES WILLIAM SWAINE 

